Silyl enol ethers are important synthetic intermediates and are widely used in a variety of reactions. Though reported ozonolysis reactions of these substrates are relatively uncommon, they typically provide the expected carbonyl cleavage product. However, silyl enol ethers are structurally and electronically related to enol ethers, which have been shown to undergo anomalous ozonolysis reactions to generate 3-alkoxy-1,2-dioxolane products. We have shown that silyl enol ethers do undergo similar reactions to enol ethers, providing 3-silyloxy- and 3-alkyl-3-silyloxy-1,2-dioxolane products in moderate to excellent yield. These dioxolane products can be further reacted to generate a variety of novel silyl protected products.

Ozonolysis of silyl enol ethers: Synthesis of 3-silyloxy-1,2- and 3-alkyl-3-silyloxy-1,2-dioxolanes

249th National Meeting (2015)

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